JP2004536916A - 固相重合によるポリカーボネート製造方法 - Google Patents
固相重合によるポリカーボネート製造方法 Download PDFInfo
- Publication number
- JP2004536916A JP2004536916A JP2003515577A JP2003515577A JP2004536916A JP 2004536916 A JP2004536916 A JP 2004536916A JP 2003515577 A JP2003515577 A JP 2003515577A JP 2003515577 A JP2003515577 A JP 2003515577A JP 2004536916 A JP2004536916 A JP 2004536916A
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- bis
- polycarbonate
- partially crystalline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 147
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 147
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 66
- 239000007787 solid Substances 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 96
- -1 diaryl carbonates Chemical class 0.000 claims abstract description 87
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 33
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 239000000155 melt Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 79
- 239000002243 precursor Substances 0.000 claims description 49
- 238000010438 heat treatment Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 239000006227 byproduct Substances 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 150000003839 salts Chemical group 0.000 claims description 14
- 229930185605 Bisphenol Natural products 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- 239000011261 inert gas Substances 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 8
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- SVOBELCYOCEECO-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)cyclohexyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=CC=2)=C1 SVOBELCYOCEECO-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 150000001449 anionic compounds Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 150000002891 organic anions Chemical class 0.000 claims description 4
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 4
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 claims description 3
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- AWNVVAMWLMUZOZ-UHFFFAOYSA-J magnesium;disodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical group [Na+].[Na+].[Mg+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O AWNVVAMWLMUZOZ-UHFFFAOYSA-J 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- NCJCOKDLOLMELX-UHFFFAOYSA-N 2-(2-hydroxyphenyl)propan-2-yl hydrogen carbonate Chemical compound CC(C=1C(O)=CC=CC1)(C)OC(O)=O NCJCOKDLOLMELX-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 58
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 13
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 3
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 3
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical group [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000003868 ammonium compounds Chemical class 0.000 claims 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 1
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 21
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000008188 pellet Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 229960001047 methyl salicylate Drugs 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- 239000002826 coolant Substances 0.000 description 6
- 239000004576 sand Substances 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000005453 pelletization Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000006384 oligomerization reaction Methods 0.000 description 4
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CC=CC(OC(Oc1ccccc1)=O)=C* Chemical compound CC=CC(OC(Oc1ccccc1)=O)=C* 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 3
- 125000005587 carbonate group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000005618 Fries rearrangement reaction Methods 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- GFVMLYBCWPLMTF-UHFFFAOYSA-N disodiomagnesium Chemical compound [Na][Mg][Na] GFVMLYBCWPLMTF-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical class C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- PYOLJOJPIPCRDP-UHFFFAOYSA-N 1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1 PYOLJOJPIPCRDP-UHFFFAOYSA-N 0.000 description 1
- CDQXVCNCQFXPSF-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[1-(2,3,5,6-tetrabromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound BrC1=C(Br)C(O)=C(Br)C(Br)=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2Br)Br)CCCCC1 CDQXVCNCQFXPSF-UHFFFAOYSA-N 0.000 description 1
- VRXQOCASOOBADQ-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[2-(2,3,5,6-tetrabromo-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound BrC=1C(Br)=C(O)C(Br)=C(Br)C=1C(C)(C)C1=C(Br)C(Br)=C(O)C(Br)=C1Br VRXQOCASOOBADQ-UHFFFAOYSA-N 0.000 description 1
- DNFSJFZWNDZYHA-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[3,3,5-trimethyl-1-(2,3,5,6-tetrabromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(Br)C(O)=C(Br)C=1Br)Br)C1=C(Br)C(Br)=C(O)C(Br)=C1Br DNFSJFZWNDZYHA-UHFFFAOYSA-N 0.000 description 1
- PBYLGADGYCTQOT-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-[1-(2,3,5,6-tetrachloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound ClC1=C(Cl)C(O)=C(Cl)C(Cl)=C1C1(C=2C(=C(Cl)C(O)=C(Cl)C=2Cl)Cl)CCCCC1 PBYLGADGYCTQOT-UHFFFAOYSA-N 0.000 description 1
- JNSWTHTUMBCINC-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-[3,3,5-trimethyl-1-(2,3,5,6-tetrachloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(Cl)C(O)=C(Cl)C=1Cl)Cl)C1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl JNSWTHTUMBCINC-UHFFFAOYSA-N 0.000 description 1
- XJFNFDUOEIPZNK-UHFFFAOYSA-N 2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)CCCCC1 XJFNFDUOEIPZNK-UHFFFAOYSA-N 0.000 description 1
- HHWOEAFLIJITGC-UHFFFAOYSA-N 2,6-dichloro-4-[1-(3,5-dichloro-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Cl)C(O)=C(Cl)C=1)C1=CC(Cl)=C(O)C(Cl)=C1 HHWOEAFLIJITGC-UHFFFAOYSA-N 0.000 description 1
- VJJCPYIHQDQHLW-UHFFFAOYSA-N 2,6-ditert-butyl-4-[1-(3,5-ditert-butyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(C=1)C(C)(C)C)C(C)(C)C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VJJCPYIHQDQHLW-UHFFFAOYSA-N 0.000 description 1
- RPLUVCHAAFRTMW-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-methylphenyl)-3,3,5-trimethylcyclohexyl]-6-methylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=C(C)C=1)C1=CC(C)=C(O)C(Br)=C1 RPLUVCHAAFRTMW-UHFFFAOYSA-N 0.000 description 1
- LTUNFYAQACHQPQ-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-phenylphenyl)-3,3,5-trimethylcyclohexyl]-6-phenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Br)C=1)C=1C=CC=CC=1)C1=CC(Br)=C(O)C(C=2C=CC=CC=2)=C1 LTUNFYAQACHQPQ-UHFFFAOYSA-N 0.000 description 1
- MLVSCWXAPGXQPH-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-phenylphenyl)cyclohexyl]-6-phenylphenol Chemical compound OC1=C(Br)C=C(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 MLVSCWXAPGXQPH-UHFFFAOYSA-N 0.000 description 1
- MDOOVKUOPDTSIM-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-propan-2-ylphenyl)-3,3,5-trimethylcyclohexyl]-6-propan-2-ylphenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C2(CC(C)(C)CC(C)C2)C=2C=C(C(O)=C(Br)C=2)C(C)C)=C1 MDOOVKUOPDTSIM-UHFFFAOYSA-N 0.000 description 1
- OWBNFSLZWKCZRB-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-propan-2-ylphenyl)cyclohexyl]-6-propan-2-ylphenol 2-tert-butyl-4-[1-(3-tert-butyl-5-chloro-4-hydroxyphenyl)cyclohexyl]-6-chlorophenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C(C)C)=C1.ClC1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Cl)C=2)C(C)(C)C)=C1 OWBNFSLZWKCZRB-UHFFFAOYSA-N 0.000 description 1
- AOJRBWSWENFQGS-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Br)C(O)=CC=C1C1(C=2C=C(Br)C(O)=CC=2)CCCCC1 AOJRBWSWENFQGS-UHFFFAOYSA-N 0.000 description 1
- IOQVTKBBXVJSDQ-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-5-tert-butyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]-6-tert-butylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Br)C=1)C(C)(C)C)C1=CC(Br)=C(O)C(C(C)(C)C)=C1 IOQVTKBBXVJSDQ-UHFFFAOYSA-N 0.000 description 1
- MTXHQKMTAGXROL-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-5-tert-butyl-4-hydroxyphenyl)cyclohexyl]-6-tert-butylphenol Chemical compound BrC1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C(C)(C)C)=C1 MTXHQKMTAGXROL-UHFFFAOYSA-N 0.000 description 1
- AKUCXWDJOMIBEH-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-4-hydroxy-5-methylphenyl)propan-2-yl]-6-methylphenol Chemical compound BrC1=C(O)C(C)=CC(C(C)(C)C=2C=C(Br)C(O)=C(C)C=2)=C1 AKUCXWDJOMIBEH-UHFFFAOYSA-N 0.000 description 1
- HSELEXDWBHMZAV-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-4-hydroxy-5-phenylphenyl)propan-2-yl]-6-phenylphenol Chemical compound C=1C(Br)=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC(Br)=C(O)C=1C1=CC=CC=C1 HSELEXDWBHMZAV-UHFFFAOYSA-N 0.000 description 1
- KCUAYENVADKTFG-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-4-hydroxy-5-propan-2-ylphenyl)propan-2-yl]-6-propan-2-ylphenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(Br)C=2)C(C)C)=C1 KCUAYENVADKTFG-UHFFFAOYSA-N 0.000 description 1
- SLQBDQGONGODHD-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-5-tert-butyl-4-hydroxyphenyl)propan-2-yl]-6-tert-butylphenol Chemical compound BrC1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(Br)C=2)C(C)(C)C)=C1 SLQBDQGONGODHD-UHFFFAOYSA-N 0.000 description 1
- QUWNLZCYRSJNMI-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxy-5-methylphenyl)cyclohexyl]-6-methylphenol Chemical compound ClC1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(Cl)C(O)=C(C)C=2)=C1 QUWNLZCYRSJNMI-UHFFFAOYSA-N 0.000 description 1
- WBVOKGXUEKNTMN-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxy-5-phenylphenyl)-3,3,5-trimethylcyclohexyl]-6-phenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Cl)C=1)C=1C=CC=CC=1)C1=CC(Cl)=C(O)C(C=2C=CC=CC=2)=C1 WBVOKGXUEKNTMN-UHFFFAOYSA-N 0.000 description 1
- SJPBRWOPJVJYBC-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxy-5-phenylphenyl)cyclohexyl]-6-phenylphenol Chemical compound OC1=C(Cl)C=C(C2(CCCCC2)C=2C=C(C(O)=C(Cl)C=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 SJPBRWOPJVJYBC-UHFFFAOYSA-N 0.000 description 1
- LWRQWMMZXJZIDD-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxy-5-propan-2-ylphenyl)cyclohexyl]-6-propan-2-ylphenol Chemical compound ClC1=C(O)C(C(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Cl)C=2)C(C)C)=C1 LWRQWMMZXJZIDD-UHFFFAOYSA-N 0.000 description 1
- NMFIMRZDSQVSRG-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Cl)C(O)=CC=1)C1=CC=C(O)C(Cl)=C1 NMFIMRZDSQVSRG-UHFFFAOYSA-N 0.000 description 1
- SANDGKAKRMRKKL-UHFFFAOYSA-N 2-chloro-4-[1-(3-chloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Cl)C(O)=CC=C1C1(C=2C=C(Cl)C(O)=CC=2)CCCCC1 SANDGKAKRMRKKL-UHFFFAOYSA-N 0.000 description 1
- ULUCDUBWKNRXIH-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxy-5-phenylphenyl)propan-2-yl]-6-phenylphenol Chemical compound C=1C(Cl)=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC(Cl)=C(O)C=1C1=CC=CC=C1 ULUCDUBWKNRXIH-UHFFFAOYSA-N 0.000 description 1
- MPEDAWUYHSAFQK-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxy-5-propan-2-ylphenyl)propan-2-yl]-6-propan-2-ylphenol Chemical compound ClC1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(Cl)C=2)C(C)C)=C1 MPEDAWUYHSAFQK-UHFFFAOYSA-N 0.000 description 1
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 1
- SQYNYXAHBZGVIP-UHFFFAOYSA-N 2-chloro-6-methyl-4-propylphenol Chemical compound CCCC1=CC(C)=C(O)C(Cl)=C1 SQYNYXAHBZGVIP-UHFFFAOYSA-N 0.000 description 1
- GUOJKHLZAXPMAC-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=CC=1)C(C)(C)C)C1=CC=C(O)C(C(C)(C)C)=C1 GUOJKHLZAXPMAC-UHFFFAOYSA-N 0.000 description 1
- TXYRFLUDJODGTP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 TXYRFLUDJODGTP-UHFFFAOYSA-N 0.000 description 1
- YOHUHRLGZRQQIM-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-5-chloro-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]-6-chlorophenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Cl)C=1)C(C)(C)C)C1=CC(Cl)=C(O)C(C(C)(C)C)=C1 YOHUHRLGZRQQIM-UHFFFAOYSA-N 0.000 description 1
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 1
- ZXBAUXQGLWEOKB-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-5-chloro-4-hydroxyphenyl)propan-2-yl]-6-chlorophenol Chemical compound ClC1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(Cl)C=2)C(C)(C)C)=C1 ZXBAUXQGLWEOKB-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 1
- BXNVUESPBYOLFC-UHFFFAOYSA-N 3,5-dibromo-4-[1-(2,6-dibromo-4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexyl]-2,6-dimethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(C)C(O)=C(C)C=1Br)Br)C1=C(Br)C(C)=C(O)C(C)=C1Br BXNVUESPBYOLFC-UHFFFAOYSA-N 0.000 description 1
- BHRBWKGEMXXTGA-UHFFFAOYSA-N 3,5-dibromo-4-[1-(2,6-dibromo-4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Br)C(C2(CCCCC2)C=2C(=C(C)C(O)=C(C)C=2Br)Br)=C1Br BHRBWKGEMXXTGA-UHFFFAOYSA-N 0.000 description 1
- WXXCYAAYVQLMDY-UHFFFAOYSA-N 3,5-dibromo-4-[2-(2,6-dibromo-4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Br)C(C(C)(C)C=2C(=C(C)C(O)=C(C)C=2Br)Br)=C1Br WXXCYAAYVQLMDY-UHFFFAOYSA-N 0.000 description 1
- XHHFWEQKCCPWLK-UHFFFAOYSA-N 3,5-dichloro-4-[1-(2,6-dichloro-4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexyl]-2,6-dimethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(C)C(O)=C(C)C=1Cl)Cl)C1=C(Cl)C(C)=C(O)C(C)=C1Cl XHHFWEQKCCPWLK-UHFFFAOYSA-N 0.000 description 1
- SXXOURCVTACNOD-UHFFFAOYSA-N 3,5-dichloro-4-[1-(2,6-dichloro-4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Cl)C(C2(CCCCC2)C=2C(=C(C)C(O)=C(C)C=2Cl)Cl)=C1Cl SXXOURCVTACNOD-UHFFFAOYSA-N 0.000 description 1
- HSRPEBYMFQNIEC-UHFFFAOYSA-N 3,5-dichloro-4-[2-(2,6-dichloro-4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Cl)C(C(C)(C)C=2C(=C(C)C(O)=C(C)C=2Cl)Cl)=C1Cl HSRPEBYMFQNIEC-UHFFFAOYSA-N 0.000 description 1
- OJTHLNYBRBMCBW-UHFFFAOYSA-N 4,4'-propane-2,2-diylbis(tetrachlorophenol) Chemical compound ClC=1C(Cl)=C(O)C(Cl)=C(Cl)C=1C(C)(C)C1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl OJTHLNYBRBMCBW-UHFFFAOYSA-N 0.000 description 1
- WUGKVYDVIGOPSI-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)-2-methylphenol Chemical group C1=C(O)C(C)=CC(C=2C=C(C)C(O)=CC=2)=C1 WUGKVYDVIGOPSI-UHFFFAOYSA-N 0.000 description 1
- BIOIMCYUMXGFMM-UHFFFAOYSA-N 4-(4-hydroxy-3-octylphenyl)-2-octylphenol Chemical group C1=C(O)C(CCCCCCCC)=CC(C=2C=C(CCCCCCCC)C(O)=CC=2)=C1 BIOIMCYUMXGFMM-UHFFFAOYSA-N 0.000 description 1
- AWKDEQSSJOJYMP-UHFFFAOYSA-N 4-[1-(4-hydroxy-2,3,5,6-tetramethylphenyl)-3,3,5-trimethylcyclohexyl]-2,3,5,6-tetramethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(C)C(O)=C(C)C=1C)C)C1=C(C)C(C)=C(O)C(C)=C1C AWKDEQSSJOJYMP-UHFFFAOYSA-N 0.000 description 1
- UVPFWYYCIQGBKX-UHFFFAOYSA-N 4-[1-(4-hydroxy-2,3,5,6-tetramethylphenyl)cyclohexyl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(O)C(C)=C(C)C(C2(CCCCC2)C=2C(=C(C)C(O)=C(C)C=2C)C)=C1C UVPFWYYCIQGBKX-UHFFFAOYSA-N 0.000 description 1
- XYVIZSMBSJIYLC-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-dimethylphenyl)-3,3,5-trimethylcyclohexyl]-2,6-dimethylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C)C(O)=C(C)C=1)C1=CC(C)=C(O)C(C)=C1 XYVIZSMBSJIYLC-UHFFFAOYSA-N 0.000 description 1
- BWCAVNWKMVHLFW-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(C)C(O)=C(C)C=2)=C1 BWCAVNWKMVHLFW-UHFFFAOYSA-N 0.000 description 1
- MOZQWEPHBHLFBF-UHFFFAOYSA-N 4-[1-(4-hydroxy-3,5-diphenylphenyl)cyclohexyl]-2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=C(C2(CCCCC2)C=2C=C(C(O)=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 MOZQWEPHBHLFBF-UHFFFAOYSA-N 0.000 description 1
- XEWPEIOKCHAXBH-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexyl]-2-methylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C)C(O)=CC=1)C1=CC=C(O)C(C)=C1 XEWPEIOKCHAXBH-UHFFFAOYSA-N 0.000 description 1
- HHMYOZSUJUQIRL-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-phenylphenyl)-3,3,5-trimethylcyclohexyl]-2-phenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=CC=1)C=1C=CC=CC=1)C1=CC=C(O)C(C=2C=CC=CC=2)=C1 HHMYOZSUJUQIRL-UHFFFAOYSA-N 0.000 description 1
- VQCOOYBPEMJQBN-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-phenylphenyl)cyclohexyl]-2-phenylphenol Chemical compound OC1=CC=C(C2(CCCCC2)C=2C=C(C(O)=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 VQCOOYBPEMJQBN-UHFFFAOYSA-N 0.000 description 1
- RYYWKBJIEBKKOP-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-propan-2-ylphenyl)-3,3,5-trimethylcyclohexyl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C2(CC(C)(C)CC(C)C2)C=2C=C(C(O)=CC=2)C(C)C)=C1 RYYWKBJIEBKKOP-UHFFFAOYSA-N 0.000 description 1
- CSNLMVVOOYVWSX-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-propan-2-ylphenyl)cyclohexyl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=CC=2)C(C)C)=C1 CSNLMVVOOYVWSX-UHFFFAOYSA-N 0.000 description 1
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 1
- BQFWXJYYZILERJ-UHFFFAOYSA-N 4-[1-[4-hydroxy-3,5-di(propan-2-yl)phenyl]-3,3,5-trimethylcyclohexyl]-2,6-di(propan-2-yl)phenol Chemical compound CC(C)C1=C(O)C(C(C)C)=CC(C2(CC(C)(C)CC(C)C2)C=2C=C(C(O)=C(C(C)C)C=2)C(C)C)=C1 BQFWXJYYZILERJ-UHFFFAOYSA-N 0.000 description 1
- GXGKCBSVGQHYDF-UHFFFAOYSA-N 4-[2-(4-hydroxy-2,3,5,6-tetramethylphenyl)propan-2-yl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(O)C(C)=C(C)C(C(C)(C)C=2C(=C(C)C(O)=C(C)C=2C)C)=C1C GXGKCBSVGQHYDF-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- ACWKCNYOCGALDS-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-diphenylphenyl)propan-2-yl]-2,6-diphenylphenol Chemical compound C=1C(C=2C=CC=CC=2)=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=C(C=1O)C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 ACWKCNYOCGALDS-UHFFFAOYSA-N 0.000 description 1
- BKTRENAPTCBBFA-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-phenylphenyl)propan-2-yl]-2-phenylphenol Chemical compound C=1C=C(O)C(C=2C=CC=CC=2)=CC=1C(C)(C)C(C=1)=CC=C(O)C=1C1=CC=CC=C1 BKTRENAPTCBBFA-UHFFFAOYSA-N 0.000 description 1
- IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 description 1
- KVZMKJCPDJQRIK-UHFFFAOYSA-N 4-[2-[4-[2-(4-hydroxy-3-methylphenyl)propan-2-yl]phenyl]propan-2-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=CC(=CC=2)C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 KVZMKJCPDJQRIK-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000408939 Atalopedes campestris Species 0.000 description 1
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 1
- PFYHAAAQPNMZHO-UHFFFAOYSA-N COC(c(cccc1)c1OC)=O Chemical compound COC(c(cccc1)c1OC)=O PFYHAAAQPNMZHO-UHFFFAOYSA-N 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N COc1ccccc1 Chemical compound COc1ccccc1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BRHFDXHJHDMDKH-UHFFFAOYSA-N ClC1C(C(CCC1)Cl)C1=C(C=CC=C1)O Chemical compound ClC1C(C(CCC1)Cl)C1=C(C=CC=C1)O BRHFDXHJHDMDKH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 229920003247 engineering thermoplastic Polymers 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000006066 glass batch Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 229960001757 magnesium disodium edta Drugs 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010671 solid-state reaction Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/911,505 US6518391B1 (en) | 2001-07-24 | 2001-07-24 | Method of polycarbonate preparation by solid state polymerization |
| PCT/US2002/019268 WO2003010219A1 (en) | 2001-07-24 | 2002-06-17 | Method of polycarbonate preparation by solid state polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004536916A true JP2004536916A (ja) | 2004-12-09 |
| JP2004536916A5 JP2004536916A5 (enExample) | 2006-01-05 |
Family
ID=25430356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515577A Pending JP2004536916A (ja) | 2001-07-24 | 2002-06-17 | 固相重合によるポリカーボネート製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6518391B1 (enExample) |
| EP (1) | EP1427771B1 (enExample) |
| JP (1) | JP2004536916A (enExample) |
| KR (1) | KR20040030840A (enExample) |
| CN (2) | CN1285641C (enExample) |
| AT (1) | ATE368700T1 (enExample) |
| DE (1) | DE60221542T2 (enExample) |
| TW (1) | TW593421B (enExample) |
| WO (1) | WO2003010219A1 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8073627B2 (en) | 2001-06-26 | 2011-12-06 | Ibis Biosciences, Inc. | System for indentification of pathogens |
| US6870025B2 (en) * | 2001-07-24 | 2005-03-22 | General Electric Company | Method of polycarbonate preparation |
| US20030139529A1 (en) * | 2001-11-02 | 2003-07-24 | General Electric Company | Method of making block copolymers by solid state polymerization |
| US7057004B2 (en) * | 2004-01-29 | 2006-06-06 | General Electric Company | Process for the production of copolycarbonates with reduced color |
| US7211641B2 (en) * | 2004-02-27 | 2007-05-01 | General Electric Company | Liquid crystal polycarbonates and methods of preparing same |
| US7041775B2 (en) * | 2004-04-20 | 2006-05-09 | General Electric Company | Method for preparing a polycarbonate oligomer mixture at low temperature for manufacturing polycarbonate |
| US7312352B2 (en) * | 2004-08-02 | 2007-12-25 | Paul William Buckley | Method of preparing ester-substituted diaryl carbonates |
| US7105626B2 (en) * | 2004-09-10 | 2006-09-12 | General Electric Company | Method for incorporating alkyl ester endgroups to improve the release properties of melt polycarbonate |
| US7132498B2 (en) * | 2004-09-27 | 2006-11-07 | General Electric Company | Process to make polycarbonate from bismethylsalicylcarbonate (BMSC) |
| US7230066B2 (en) * | 2004-12-16 | 2007-06-12 | General Electric Company | Polycarbonate—ultem block copolymers |
| EA012678B1 (ru) * | 2005-05-26 | 2009-12-30 | Гала Индастриз, Инк. | Способ и устройство для получения кристаллических полимерных гранул и зерен |
| US9032641B2 (en) | 2005-05-26 | 2015-05-19 | Gala Industries, Inc. | Method and apparatus for making crystalline polymeric pellets and granules |
| US7521119B2 (en) * | 2005-07-07 | 2009-04-21 | Sabic Innovative Plastics Ip B.V. | Windows and other articles made from DMBPC polycarbonate homopolymer and copolymer |
| US7365149B2 (en) * | 2005-12-12 | 2008-04-29 | Hans-Peter Brack | Equipment cleaning in the manufacture of polycarbonates |
| US7485695B2 (en) * | 2005-12-21 | 2009-02-03 | Sabic Innovative Plastics Ip B.V | Polycarbonates containing low levels of methyl salicylate prepared by a melt polymerization in a reactive extruder |
| US7485694B2 (en) * | 2005-12-21 | 2009-02-03 | Sabic Innovative Plastics Ip B.V. | Polycarbonates containing low levels of methyl salicylate prepared by a melt polymerization in a reactive extruder |
| US7498399B2 (en) * | 2006-05-31 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Method of preparing ester-substituted diaryl carbonates |
| US7495064B2 (en) * | 2006-06-26 | 2009-02-24 | Sabic Innovative Plastics Ip Bv | Manufacture of polycarbonates |
| US7482423B2 (en) * | 2006-06-30 | 2009-01-27 | Sabic Innovative Plastics Ip B.V. | Polycarbonates and method of preparing same |
| US7541420B2 (en) * | 2006-06-30 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Method for making molded polycarbonate articles with improved color |
| US7498400B2 (en) * | 2006-06-30 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Method of preparing polycarbonate |
| US7645851B2 (en) * | 2006-06-30 | 2010-01-12 | Sabic Innovative Plastics Ip B.V. | Polycarbonate with reduced color |
| US20080254299A1 (en) * | 2007-04-13 | 2008-10-16 | General Electric Company | Scratch-resistant Layered Composite and Articles |
| US7666977B2 (en) * | 2007-05-03 | 2010-02-23 | Sabic Innovative Plastics Ip B.V. | Poly(carbonate-co-urea) copolymers and melt transesterification method of preparing these copolymers |
| US7557175B2 (en) * | 2007-05-03 | 2009-07-07 | Sabic Innovative Plastics Ip B.V. | Poly(carbonate-co-urea) copolymers and melt transesterification method of preparing these copolymers |
| US20080287640A1 (en) * | 2007-05-15 | 2008-11-20 | General Electric Company | Process for the production of polycarbonate using an ester substituted diaryl carbonate |
| US7601794B2 (en) * | 2007-09-28 | 2009-10-13 | Sabic Innovative Plastics Ip B.V. | Monomer solution for producing polycarbonate |
| US7619053B2 (en) * | 2007-09-28 | 2009-11-17 | Sabic Innovative Plastics Ip B.V. | Monomer solution for producing polycarbonate |
| US7632913B2 (en) * | 2007-09-28 | 2009-12-15 | Sabic Innovative Plastics Ip B.V. | Method of producing polycarbonate in a flash devolatilization system |
| US7615605B2 (en) * | 2008-03-26 | 2009-11-10 | Sabic Innovative Plastics Ip B.V. | Monomer solution for producing polycarbonate |
| US7671165B2 (en) * | 2008-05-16 | 2010-03-02 | Sabic Innovative Plastics Ip B.V. | Method of forming polycarbonate |
| US7674872B2 (en) * | 2008-06-17 | 2010-03-09 | Sabic Innovative Plastics Ip B.V. | Method of producing high molecular weight polymer |
| US7547799B1 (en) | 2008-06-20 | 2009-06-16 | Sabic Innovative Plastics Ip B.V. | Method for producing phenolic compound |
| US8058469B2 (en) * | 2008-11-03 | 2011-11-15 | Sabic Innovative Plastics Ip B.V. | Method for making carbamates, ureas and isocyanates |
| US7977447B2 (en) * | 2008-11-18 | 2011-07-12 | Sabic Innovative Plastics Ip B.V. | Method for making carbonates and esters |
| US7659359B1 (en) | 2008-11-18 | 2010-02-09 | Sabic Innovative Plastics Ip B.V. | Stabilization of isosorbide-based polycarbonate |
| US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
| KR101447269B1 (ko) * | 2011-11-21 | 2014-10-06 | 제일모직주식회사 | 폴리카보네이트, 그 제조방법 및 이를 포함하는 광학필름 |
| CN106117534B (zh) * | 2016-05-19 | 2017-11-17 | 福建盈科百创电子有限公司 | 一种安防用阻燃聚碳酸酯材料及其生产工艺 |
| EP3398927B1 (en) * | 2017-05-04 | 2019-11-13 | SABIC Global Technologies B.V. | Method of forming and using a bisphenol oil stream |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323668A (en) | 1980-12-03 | 1982-04-06 | General Electric Company | (Ortho-alkoxycarbonyaryl)-carbonate transesterification |
| US5717056A (en) * | 1996-05-24 | 1998-02-10 | General Electric Company | Method for preparing polycarbonate by solid state polymerization |
| US6410777B1 (en) * | 1997-04-04 | 2002-06-25 | Teijin Limited | Salicylic acid ester derivative and its production |
| US5905135A (en) | 1997-12-08 | 1999-05-18 | General Electric Company | Method of preparing polycarbonates by solid state polymerization |
| JP4286914B2 (ja) * | 1998-03-17 | 2009-07-01 | 帝人株式会社 | 芳香族ポリカーボネートの製造方法 |
| CN1233625A (zh) * | 1998-04-30 | 1999-11-03 | 通用电气公司 | 芳香聚碳酸酯再回收的方法 |
| CN1233623A (zh) * | 1998-04-30 | 1999-11-03 | 通用电气公司 | 用固态聚合制备聚碳酸酯的方法 |
| US6143859A (en) | 1999-08-09 | 2000-11-07 | General Electric Company | Copolycarbonate preparation by solid state polymerization |
| US6031063A (en) | 1999-08-09 | 2000-02-29 | General Electric Company | Method for enhancing crystallinity of polycarbonates |
| US6255435B1 (en) * | 1999-08-10 | 2001-07-03 | General Electric Company | Method of crystallizing polycarbonate prepolymer |
| EP1245607A4 (en) * | 1999-09-22 | 2004-11-10 | Teijin Ltd | PROCESS FOR CRYSTALLIZING LOW MOLECULAR WEIGHT POLYCARBONATE AND PROCESS FOR PRODUCING POLYCARBONATE RESIN FROM POLYCARBONATE OBTAINED THEREBY |
-
2001
- 2001-07-24 US US09/911,505 patent/US6518391B1/en not_active Expired - Fee Related
-
2002
- 2002-06-17 WO PCT/US2002/019268 patent/WO2003010219A1/en not_active Ceased
- 2002-06-17 AT AT02756220T patent/ATE368700T1/de not_active IP Right Cessation
- 2002-06-17 JP JP2003515577A patent/JP2004536916A/ja active Pending
- 2002-06-17 DE DE60221542T patent/DE60221542T2/de not_active Expired - Fee Related
- 2002-06-17 KR KR10-2004-7000970A patent/KR20040030840A/ko not_active Abandoned
- 2002-06-17 CN CNB028186826A patent/CN1285641C/zh not_active Expired - Fee Related
- 2002-06-17 EP EP02756220A patent/EP1427771B1/en not_active Expired - Lifetime
- 2002-06-17 CN CNB2005101295472A patent/CN100384905C/zh not_active Expired - Fee Related
- 2002-07-11 TW TW091115451A patent/TW593421B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040030840A (ko) | 2004-04-09 |
| DE60221542D1 (de) | 2007-09-13 |
| CN1558923A (zh) | 2004-12-29 |
| TW593421B (en) | 2004-06-21 |
| US6518391B1 (en) | 2003-02-11 |
| ATE368700T1 (de) | 2007-08-15 |
| CN100384905C (zh) | 2008-04-30 |
| EP1427771A1 (en) | 2004-06-16 |
| WO2003010219A1 (en) | 2003-02-06 |
| DE60221542T2 (de) | 2008-04-30 |
| CN1789306A (zh) | 2006-06-21 |
| EP1427771B1 (en) | 2007-08-01 |
| CN1285641C (zh) | 2006-11-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1427771B1 (en) | Method of polycarbonate preparation by solid state polymerization | |
| EP1577333B1 (en) | Method of polycarbonate preparation | |
| KR100874297B1 (ko) | 폴리카보네이트를 제조하기 위한 압출 방법 | |
| US6420512B1 (en) | Extrusion method for making polycarbonate | |
| US7115700B2 (en) | Method of polycarbonate preparation | |
| EP0403657B1 (en) | A porous, crystallized, aromatic polycarbonate prepolymer, a porous, crystallized aromatic polycarbonate, and production methods | |
| JP4057420B2 (ja) | 溶融ポリカーボネート触媒系 | |
| EP2052009B1 (en) | Method of preparing polycarbonate | |
| JP2005508419A (ja) | 固相重合によるブロックコポリマーの製造方法 | |
| JP3208210B2 (ja) | 結晶性芳香族ポリカーボネートプレポリマーの製造方法及び芳香族ポリカーボネートの製造方法 | |
| US7629432B2 (en) | Tert-butylhydroquinone polycarbonates | |
| WO2008051849A1 (en) | Tert-butylhydroquinone polycarbonates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050615 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050615 |
|
| RD12 | Notification of acceptance of power of sub attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7432 Effective date: 20071101 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080208 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080219 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080519 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20090623 |